The invention relates to certain thiophene sulfonamide compounds having alkenyl substituents ortho to the sulfonylurea linkage, agriculturally suitable compositions thereof and method of their use as herbicides or plant growth regulants.
In the most common situation, the control of undesired vegetation is desired to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,368,069 discloses herbicidal benzenesulfonamides of formula ##STR1## wherein R is --(CR.sub.5 R.sub.6).sub.n --R.sub.2 ;
n is 0 or 1; and PA1 R.sub.2 may be C.sub.5 -C.sub.6 cycloalkenyl or C.sub.2 -C.sub.5 alkenyl. PA1 R is, among others, a variety of alkyl or substituted alkyl groups. PA1 R.sub.9 is H or C.sub.1 -C.sub.3 alkyl. PA1 R.sub.6 is H, C.sub.1 -C.sub.4 alkyl or fluorine; PA1 R.sub.7 is H or CH.sub.3 ; PA1 X is O, S, SO or SO.sub.2 ; PA1 R.sub.8 may be C.sub.2 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 alkynyl, etc. PA1 R.sub.1 and R.sub.2 are independently H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, which are optionally substituted by 1-3 halogen atoms, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfenyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, OH, etc. PA1 R.sub.2 is ##STR9## PA1 n is 0 or 1; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CN, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl or CO.sub.2 R.sup.III ; PA1 R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA1 R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA1 R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA1 W is W.sub.1 ; PA1 W.sub.1 is C.sub.2 -C.sub.8 alkenyl substituted with 1-3 atoms of F, Cl or Br; PA1 A is ##STR12## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, ##STR13## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.6 is H or CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA1 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; and PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 OCH.sub.3 ; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when X or Y is OCF.sub.2 H then Z is CH; PA1 (c) the W substituent and the sulfonylurea bridge are on adjacent carbon atoms; PA1 (d) when W.sub.3 is S, then R is H, A is A-1, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 or CH(OCH.sub.3).sub.2 ; and PA1 (e) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two and the number of carbons of W must be less than or equal to four. PA1 (f) when R is H, W.sub.3 is O, n is O, R.sub.1 is H, A is A-1, X is CH.sub.3 or OCH.sub.3 and Y is CH.sub.3 or OCH.sub.3, then W.sub.1 is other than C.sub.2 alkenyl substituted by 3 Cl and/or 3 F. PA1 W.sub.3 is O; PA1 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl or CO.sub.2 R.sup.III ; PA1 W.sub.1 is C.sub.2 -C.sub.5 alkenyl substituted with 1-3 atoms of F, Cl or Br; PA1 A is A-1, A-2, A-3, A-4, A-5 or A-6; and PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, ##STR14## or N(OCH.sub.3)CH.sub.3 PA1 R is H; and PA1 W.sub.3 is O. PA1 R.sub.1 is H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3, and is not para to the sulfonylurea bridge. PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl, F, Br, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and PA1 Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OC.sub.2 H.sub.5, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3. PA1 W.sub.1 is C.sub.2 -C.sub.5 alkenyl substituted by 1-3 atoms of F, Cl or Br. PA1 A is A-1; PA1 X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, Cl or OCF.sub.2 H; PA1 Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, OCF.sub.2 H, NHCH.sub.3, N(CH.sub.3).sub.2 or cyclopropyl; and PA1 R.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl. PA1 "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publishers, Inc., New York and London; PA1 "Pyrimidines", Vol. 16 of the same series by D. J. Brown; PA1 "s-Triazines and Derivatives", Vol. 13 of the same series by E. M. Smolin and L. Rapaport; and PA1 F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963), which describe the synthesis of triazines. PA1 H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; PA1 R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; PA1 H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; PA1 G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and PA1 J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
South African Patent Application No. 83/3779 discloses herbicidal sulfonamides of formula ##STR2## wherein A is a radical of the formula C.dbd.CR; and
Herbicidal thiophene sulfonamides are disclosed in European Patent Application (EP-A) No. 30,142, published June 10, 1981.
Herbicidal pyridinesulfonamides are disclosed in European Patent Application (EP-A) No. 13,480, published July 23, 1980.
U.S. Pat. No. 4,420,325 discloses herbicidal sulfonamides of the following formula ##STR3## wherein R.sub.1 is F, Cl, Br, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkyl, NO.sub.2, CO.sub.2 R.sub.4, SO.sub.2 R.sub.5, SO.sub.2 NR.sub.6 R.sub.7, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 CH.sub.2 CF.sub.3, OSO.sub.2 R.sub.5 or CH.sub.2 L; and
South African Patent Application No. 84/2722, published 10/13/84, discloses herbicidal sulfonamides of formula ##STR4## wherein A is a radical of formula --CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
South African Patent Application No. 84/6610 discloses herbicidal pyrazolesulfonylureas of formula ##STR5## wherein X is O or NR.sub.6 ;
South African Patent Application No. 83/6449, published 3/1/84, discloses herbicidal sulfonylureas of the formula ##STR6## wherein R.sub.3 is C.sub.2 -C.sub.10 alkenyl which is substituted by, inter alia, one or more fluorine or bromine atoms or by one or more hydroxyl, cyano or nitro groups.
European Publication No. 132,230, published 1/23/85, discloses a process for preparing sulfonylureas of the formula ##STR7## wherein T denotes a substituted phenyl radical of formula ##STR8## X is, inter alia, H, halogen, C.sub.2 -C.sub.4 alkynyl; R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; and
U.S. Pat. No. 4,620,868 discloses substituted thiophenesulfonylurea compounds where the substitution as an ethenyl or propenyl group having all hydrogen atoms replaced by chlorine and/or fluorine atoms.